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Related Concept Videos

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene π orbitals.
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.

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Related Experiment Video

Updated: Jun 27, 2026

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

Ligand-controlled sequential activation enables nickel-catalysed alkyl-alkynyl coupling.

Nayeong Kim1, Hyeri Jeon1,2, Seungwoo Hong3,4

  • 1Department of Chemistry and Nanoscience, Ewha Womans University, Seoul, Republic of Korea.

Nature Communications
|June 25, 2026
PubMed
Summary

A new nickel-catalyzed reaction enables direct alkynyl-alkyl bond formation using unactivated alkyl halides. A specialized ligand controls activation sequence, overcoming reactivity mismatches for efficient carbon-carbon bond construction.

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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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Published on: May 28, 2014

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cross-electrophile coupling between alkyl and alkynyl halides is difficult due to reactivity differences.
  • Existing methods struggle with selectivity and activating unreactive substrates.

Purpose of the Study:

  • To develop a nickel-catalyzed method for direct alkynyl-alkyl bond formation.
  • To overcome challenges associated with reactivity mismatch and chemoselectivity in cross-electrophile couplings.

Main Methods:

  • Utilized a nickel catalyst with a specifically designed tridentate ligand.
  • Investigated sequential electrophile activation pathways.
  • Employed mechanistic studies to understand the reaction mechanism.

Main Results:

  • Achieved direct construction of internal alkynes from unactivated primary, secondary, and tertiary alkyl halides.
  • Demonstrated broad functional-group tolerance.
  • Enabled reductive coupling of tertiary alkyl electrophiles with alkynyl partners.
  • Identified an alkyl-first activation mode mediated by the tridentate ligand.

Conclusions:

  • The tridentate ligand controls electrophile activation sequence, enabling challenging C-C bond formation.
  • This ligand-controlled strategy expands the scope of alkynyl-alkyl coupling.
  • The alkyl-first activation pathway enhances chemoselectivity and suppresses homocoupling.